Madeleinol B

Details

• Internal ID: b6eca2e6-b37e-4af9-9a16-bd05776d75d9
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans
• IUPAC Name: 2-methyl-1-[3,5,7-trihydroxy-2-methyl-2-(4-methylpent-3-enyl)-3,4-dihydrochromen-8-yl]propan-1-one
• SMILES (Canonical): CC(C)C(=O)C1=C(C=C(C2=C1OC(C(C2)O)(C)CCC=C(C)C)O)O
• SMILES (Isomeric): CC(C)C(=O)C1=C(C=C(C2=C1OC(C(C2)O)(C)CCC=C(C)C)O)O
• InChI: InChI=1S/C20H28O5/c1-11(2)7-6-8-20(5)16(23)9-13-14(21)10-15(22)17(19(13)25-20)18(24)12(3)4/h7,10,12,16,21-23H,6,8-9H2,1-5H3
• InChI Key: OTCGNFYHXWMHCW-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₅
• Molecular Weight: 348.40 g/mol
• Exact Mass: 348.19367399 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 3.74
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• CHEMBL3613752
• 2-methyl-1-[3,5,7-trihydroxy-2-methyl-2-(4-methylpent-3-enyl)chroman-8-yl]propan-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9835	98.35%
Caco-2	+	0.7156	71.56%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6551	65.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8593	85.93%
OATP1B3 inhibitior	+	0.8992	89.92%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7564	75.64%
BSEP inhibitior	-	0.6162	61.62%
P-glycoprotein inhibitior	-	0.7286	72.86%
P-glycoprotein substrate	-	0.6376	63.76%
CYP3A4 substrate	+	0.5583	55.83%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.7900	79.00%
CYP3A4 inhibition	-	0.6362	63.62%
CYP2C9 inhibition	-	0.6935	69.35%
CYP2C19 inhibition	-	0.5058	50.58%
CYP2D6 inhibition	-	0.8514	85.14%
CYP1A2 inhibition	+	0.6732	67.32%
CYP2C8 inhibition	-	0.7889	78.89%
CYP inhibitory promiscuity	-	0.7019	70.19%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7256	72.56%
Eye corrosion	-	0.9931	99.31%
Eye irritation	-	0.5843	58.43%
Skin irritation	-	0.6193	61.93%
Skin corrosion	-	0.9392	93.92%
Ames mutagenesis	-	0.7154	71.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5275	52.75%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.7725	77.25%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.5747	57.47%
Acute Oral Toxicity (c)	III	0.4744	47.44%
Estrogen receptor binding	+	0.7498	74.98%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.7153	71.53%
Glucocorticoid receptor binding	+	0.8938	89.38%
Aromatase binding	+	0.5966	59.66%
PPAR gamma	+	0.7640	76.40%
Honey bee toxicity	-	0.8154	81.54%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9904	99.04%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.77%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.04%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.12%	94.45%
CHEMBL2581	P07339	Cathepsin D	94.61%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	92.39%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.42%	89.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.00%	91.24%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.39%	90.71%
CHEMBL221	P23219	Cyclooxygenase-1	83.85%	90.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.48%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.11%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.52%	99.17%

Plants that contains it

• Hypericum roeperianum

Cross-Links

• PubChem: 78073027
• LOTUS: LTS0174228
• wikiData: Q105199483